CN101754967A

CN101754967A - 苯并咪唑聚(adp-核糖)聚合酶抑制剂

苯并咪唑聚(adp-核糖)聚合酶抑制剂 Download PDF

Info

Publication number: CN101754967A
Authority: CN; China
Prior art keywords: bases; benzimidazole; carboxamides; thiophene; pyrrolidin
Prior art date: 2007-07-16
Legal status : Pending

Application number

CN200880025066A

Other languages

English (en)

Chinese (zh)

Inventor

V·B·甘地

V·L·吉兰达

龚建春

T·D·彭宁

朱贵东

Current Assignee

AbbVie Inc

Original Assignee

Abbott GmbH and Co KG

Priority date

2007-07-16

Filing date

2008-07-16

Publication date

2010-06-23

2008-07-16 Application filed by Abbott GmbH and Co KG filed Critical Abbott GmbH and Co KG

2010-06-23 Publication of CN101754967A publication Critical patent/CN101754967A/zh

Status Pending legal-status Critical Current

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PWJFNRJRHXWEPT-UHFFFAOYSA-N ADP ribose Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OCC(O)C(O)C(O)C=O)C(O)C1O PWJFNRJRHXWEPT-UHFFFAOYSA-N 0.000 title abstract 2
SRNWOUGRCWSEMX-KEOHHSTQSA-N ADP-beta-D-ribose Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=2N=CN=C(C=2N=C1)N)OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O SRNWOUGRCWSEMX-KEOHHSTQSA-N 0.000 title abstract 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
SEKJSSBJKFLZIT-UHFFFAOYSA-N LSM-1988 Chemical compound C1=CC(CN(C)C)=CC=C1C1=NC2=CC=CC3=C2N1CCNC3=O SEKJSSBJKFLZIT-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 114
238000000034 method Methods 0.000 claims abstract description 15
-1 heteroaryl hydrocarbon Chemical class 0.000 claims description 256
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 195
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 147
125000000753 cycloalkyl group Chemical group 0.000 claims description 104
229930192474 thiophene Natural products 0.000 claims description 72
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 71
239000004215 Carbon black (E152) Substances 0.000 claims description 68
150000001925 cycloalkenes Chemical class 0.000 claims description 68
229930195733 hydrocarbon Natural products 0.000 claims description 68
125000000217 alkyl group Chemical group 0.000 claims description 54
125000001424 substituent group Chemical group 0.000 claims description 52
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 47
125000003342 alkenyl group Chemical group 0.000 claims description 46
125000001072 heteroaryl group Chemical group 0.000 claims description 41
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 35
229910052794 bromium Inorganic materials 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 31
229910052740 iodine Inorganic materials 0.000 claims description 31
229910052731 fluorine Inorganic materials 0.000 claims description 29
125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 23
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 23
238000006467 substitution reaction Methods 0.000 claims description 22
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
206010028980 Neoplasm Diseases 0.000 claims description 21
229910006074 SO2NH2 Inorganic materials 0.000 claims description 21
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 21
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
201000011510 cancer Diseases 0.000 claims description 14
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 12
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
238000001959 radiotherapy Methods 0.000 claims description 8
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 7
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 7
OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
YQOPNAOQGQSUHF-UHFFFAOYSA-N 1-propan-2-ylpyrrolidine Chemical compound CC(C)N1CCCC1 YQOPNAOQGQSUHF-UHFFFAOYSA-N 0.000 claims description 6
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
229910052697 platinum Inorganic materials 0.000 claims description 6
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 5
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 5
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
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229960002949 fluorouracil Drugs 0.000 claims description 5
BNUVOMNEUJWHCF-SSDOTTSWSA-N (2r)-2-thiophen-2-ylpyrrolidine Chemical compound C1CCN[C@H]1C1=CC=CS1 BNUVOMNEUJWHCF-SSDOTTSWSA-N 0.000 claims description 4
IRHBPLJGCWXMPV-UHFFFAOYSA-N 2-thiophen-2-ylpiperidine Chemical compound N1CCCCC1C1=CC=CS1 IRHBPLJGCWXMPV-UHFFFAOYSA-N 0.000 claims description 4
BNUVOMNEUJWHCF-UHFFFAOYSA-N 2-thiophen-2-ylpyrrolidine Chemical compound C1CCNC1C1=CC=CS1 BNUVOMNEUJWHCF-UHFFFAOYSA-N 0.000 claims description 4
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
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125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 4
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 3
ZHBLIWDUZHFSJW-UHFFFAOYSA-N 3-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2C=NC=CC=2)=C1 ZHBLIWDUZHFSJW-UHFFFAOYSA-N 0.000 claims description 3
KHTGYJRTNNIIBM-UHFFFAOYSA-N 4-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2C=CN=CC=2)=C1 KHTGYJRTNNIIBM-UHFFFAOYSA-N 0.000 claims description 3
PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical class CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 claims description 3
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 3
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
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BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims description 3
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SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 3
229960001924 melphalan Drugs 0.000 claims description 3
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 3
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VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 2
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